The Road Not Taken
by ErisChaos04
Summary: Edward Kenway left Bristol to find the means to make a better life for his wife, Caroline. A wife who left him despite the fact she was his reason for the madness he pursued. He left anyway. Along the way, he crossed the Templars, became an unwitting ally to the Assassins, met James Kidd (Mary?), and what was this about an Observatory? Edward found a life he never expected.
1. Chapter 1

_Two roads diverged in a yellow wood, And sorry I could not travel both And be one traveler, long I stood And looked down one as far as I could To where it bent in the undergrowth; Then took the other, as just as fair, And having perhaps the better claim, Because it was grassy and wanted wear; Though as for that the passing there Had worn them really about the same, And both that morning equally lay In leaves no step had trodden black. Oh, I kept the first for another day! Yet knowing how way leads on to way, I doubted if I should ever come back. I shall be telling this with a sigh Somewhere ages and ages hence: Two roads diverged in a wood, and I- I took the one less traveled by, And that has made all the difference._

 _"The Road Not Taken" -Robert Frost_

Edward Kenway stood at the help of his ship, The Jackdaw, looking out at the vastness that was the West Indies. The smell of sea salt filled his nose and the sea breeze whipped at his sandy colored hair. In some ways, he was very content with where his life was currently. Other ways, not so much.

He had, quite frankly, been hurdled into an unknown part of the world he'd never imagined. After killing Duncan Walpole, and assuming his identity, Edward figured he'd complete some shady job and be on his way. Rather, that shady job catapulted him into an underworld he had no idea existed. But also, Edward found, for the first time, something to truly fight for. He knew very little of who these Templar bastards were, or who these Assassins—the so-called, self-appointed heroes and saviors—were, but he did know he barely trusted either side. He, however, unwittingly threw in his lot with the Assassins. He didn't particularly trust them, but they were the far lesser of 2 evils.

What had been promised to his wife as a 2-year privateering gig turned into a much grander scheme than he could have ever fathomed before. He missed Caroline, his wife, dearly, but this seemed to promise him so much more. Not to mention, the end of the Spanish War meant the end of privateering. Edward, and many others like him, found themselves without a job, money, or anywhere to go. So many found their own ships and crews and took to the seas on their own accords.

Of course, now they had to dodge the British Royal Navy, rather than work alongside it, but Edward didn't give a damn. All that mattered to him was his own neck and his own pocket. Murder ("assassinations"), theft, pickpocketing, lying, cheating, stealing, he wasn't above doing any of that. If it got him where he wanted to go, he had no qualms with any of it.

But what did he want? It was simple, really: wealth, fortune, and a name that indicated a well-recognized gentleman of quality, not the local drunk. Even as a child, his name meant little more than being a shamed, poor child born to poverty with no hope of ever achieving a station. He had been doomed from day one.

But not anymore. Edward Kenway would become a man of means. Even if it meant posing as a part of the mercantile class down the road, fine. He didn't want to be the town drunk anymore.

"Lost in thought are we?" a voice said, breaking Edward's focus. James.

"Aye," Edward said.

"Home, the Missus, or your future fortune?"

"All 3 I suppose."

"For someone wanting to be seen as a threat, you are quite the brooding fellow," James answered.

"I suppose you're right," he answered, "but unlike most of the other men on the seas, I have a deeper motivation than plunder and women…though those things have their place."

Edward smirked at his own last comment. James smiled.

"You have a point," he answered.

James Kidd was the one Assassin that Edward genuinely liked. Like all assassins, James had his reasons for why he joined, but he wasn't some high and mighty, holier than thou type, either. He hadn't let the mission of the Assassins turn him into someone with a sainthood complex. If anything, James just wanted to do the best he could with what he had. Edward could respect that, even if that was still a bit high minded for him.

Not to mention, James was the only one who took the time to explain this guild of freedom fighters. Of course, he didn't have all of the answers, but he happily shared the few answers he did have. It was more than most of these sanctimonious bastards offered, so Edward took it.

"Nothing is true, everything is permitted."

Edward definitely liked the sound of that.

"The lads on deck getting to be a bit much?" Edward asked.

"Aye," James said, "but nothing unforgivable. Just like the quiet of the helm."

"I'm not sure Adé is someone I would describe as quiet," Edward teased. Adéwalé, the former slave-turned-quartermaster barely smiled, but Edward was used to his stony demeanor. After living so many years as a slave, Edward didn't blame him. Hell, he wasn't sure if it were possible for a former slave to be any other way.

"Somber, but not quiet," Adé said, teasing himself. Edward and James chuckled.

"Can't be quiet with a crew like this," Edward said, "but they're good men."

"When they're sober," James added.

"Suppose you're right," Edward answered.

They had decided to come back to Nassau for a spell, and James had hoped aboard for the rare ride on the Jackdaw. The crew was in need of a break before heading off on more important business. Edward wouldn't admit it, but he was even rather fatigued. Their recent weeks at sea had been particularly rough. There had been a hurricane, and general stormy weather. The few hours Edward was able to rest in his cabin were the loneliest he'd have at any given time. He never grew accustomed to sleeping alone, even if his parting from his wife had been less than ideal. He loved and missed her just the same.

In Edward's mind, he did all of this for her. He wanted to be a respectable husband. One she could be proud of.

At the tavern that night, Edward sat at the bar nursing a beer while his men made fools of themselves with the local "dancers." Other patrons jeered the men on as they shoved coins down the front of the girls' dresses. Edward thought back to his days in Bristol. He wouldn't call himself a "reformed" man, but his days of drinking and whoring were behind him. That life had no interest for him anymore. Besides, Edward was a mean drunk. It got him in trouble more often than not. And Edward had enough trouble on his hands as it was.

"Still brooding are we?" James asked, taking a bar stool next to Edward. Edward smiled a bit.

"I suppose," he said.

"Not to worry," James said, "happens to the best of us."

"Assuming that means it happens to you?" Edward replied, that sarcastic smirk appearing again.

"I suppose I am," James quipped in return. Edward laughed.

"I like you, James," he said, "not sure about the rest of your vigilante friends, but you're a good man."

"Suppose that's the closest to a compliment I'll ever get out of you."

"So you had better take it," Edward replied as he took a drink.

"I most definitely do."

Edward and James stayed relatively quiet after that. They chewed at conversation, but nothing with much substance. It finally hit Edward how tired he was, so he opted to pay for a room for the night and sleep on dry land for a change.

As he trudged up to his room and shrugged out of his coat, the insanity of the day subsided. His thought began to clear and they wandered back to the most important part of his life…

Caroline…

Always and forever, Caroline…


	2. Chapter 2

Edward elected to stay in Nassau for a few weeks before heading to Jamaica, giving himself and his crew a chance to rest. Edward needed to catch up with his associates in Nassau—both pirate and Assassin.

Blackbeard was on about needing medicine to help the ailing community and apparently there was a shipwreck near Charles-towne that had medicine on it when the ship went under. Edward had yet to travel that far north, but it was beginning to sound more and more like it was inevitable. There was talk concerning Laureano Torres, the governor of Havana, dealing with a Dutch slave trader, Laurence Prins, floating around the settlement as well. To be honest, Edward was starting to feel like he was burning the candle at both ends. But, he had little choice. Both pirates and Assassins were means to the ends of discovering and understanding the Observatory.

Edward wasn't sure why he still felt so driven to find it. Maybe he valued some kind of privacy and liberty for mankind. Pirates in Nassau were always talking about man's true nature, and freedom, and liberty. It all sounded just fine to Edward. For far too long the common man had suffered for the whims of the upper classes and for what? To continue living in squalor? To keep apologizing for not being born into opportunity? Why should a few fops at the top reap all of the benefits of the hard work of many?

Maybe Edward was more idealistic than he gave himself credit for.

Adé and Edward had been bickering back and forth, bringing Edward's attention back to the matter at hand. Edward was determined to find this Observatory, and make them all rich. Adé didn't doubt Edward, but there was a hitch in all of this for him, what with being a former slave and having to now make a shady deal with a trader. Since taking his fortress, Edward had been after the governor of Havanna, as well as Prins. Word was, this man the Assassin's were after—"the Sage"—was in the care of Prins. Edward was going to make it a point to find and 'liberate' the Sage, find the Observatory, and make out like the pirates they were, before heading back home.

"Not if young Master Kidd doesn't get to him first," Adé said, nodding over Edward's shoulder, ending their fight. Edward turned, and saw the familiar red bandana. He had to think fast.

"He's here to kill Prins," Edward said, and darted off after Kidd.

Edward made it undetected over to James, ducked next to him and touched his shoulder. James jumped and turned to see Edward.

"Christ, Kenway," James said, "I almost killed you!"

"But you didn't," Edward said, "now hold back. No sudden moves, we're tracking them and their deal."

"Now is our chance!"

"Not until we see the Sage."

James relented, and went with Edward to track both men, instead of killing them straight away. They had to see the Sage, or at least, Edward did. It was almost as if Laurence knew they were being followed. But, they continued on, waiting on Torres to give the ransom to Prins like he was supposed to. And that's when all hell broke loose.

Prins HAD figured it out, and sent his guards after Edward and James. They were able to fend off the guards well enough to survive, but it meant they had to run. There was no way they would live to see the end of this if they stayed.

James also lost BOTH of his kills, and was none too thrilled about it. Edward was at least able to talk him down, and promised both kills. James was more that positive Edward intended to keep his word, and that was the only thing keeping him from tearing Edward's throat out.

However, if Edward was going to make James wait on his kills, then James wanted help as soon as they had a pinpoint on the Sage. Edward found it fair, but before he could say anything at all, James stormed off, visibly angry and barely thinking straight. Edward sighed, not sure of what to do next. He decided for now he would head to his ship, and figure out what next.

A few days later, Edward received word to meet James in Kingston. Very specific directions at that: There was a certain windmill that James would be at in 2 weeks' time, which was also near Prins' residence.

"Well that settles that," Edward said to Adé after reading the message. "Head for Kingston. James has it sorted."

"If that's what you want," Adé answered, none too thrilled. Edward knew Adé's feelings by this point in the game. The crew, however, was ready to go. They had been in Nassau for weeks now. It was time for something new.

The _Jackdaw_ made good time to Kingston, and Edward was a few days early. As soon as he made it off of the ship, he saw Prins' mansion on the horizon, and a windmill nearby. That must be the place.

James had said to meet 2 days from this point. Edward figured he should scout the town, and see what his "outs" would be in case things went sideways. This wasn't his first time in Kingston, but it WAS his first time here on such important business. Best to be careful.

Two days later, just before the sun started to set, Edward made his way to the windmill. A slight silhouette was already sitting atop the structure, staring off into the distance. Edward scaled the side of the building, and balanced his way across the top, joining James at the top.

"Evening," he said as Edward got comfortable.

"That it is," Edward replied, sitting down. "Suppose we couldn't meet in a pub?"

"I came to Kingston chasing a target," James said, "getting pissed ain't a priority."

Edward and James discussed the situation. Edward was more than happy to work together alongside James. He wanted Prins, Edward wanted the Sage. James didn't argue, however, he did inform Edward that the Assassins wanted the Sage too, and Edward needed to watch his back. Edward understood. He may not be chummy with the Assassins, but he wasn't looking to obstruct them either.

"May the best man win," Edward said. James looked off into the horizon again, at the mansion before them.

"There's guards patrolling that property from end to end. Looks to me like they use bells to signal trouble. See there? We'll want to disable those before pushing too far. With so many men about, we can't rely on stealth alone, so I'll do what I can to distract and draw their attention."

As he said that, James reached behind him, and grabbed his knife. Edward looked over the property at all the bells to see what they were up against. He looked back at James to make a comment, but to his surprise, it wasn't a "James" sitting next to him anymore.

"Your name's not James is it?" Edward asked, looking at her (him?) contemplatively, trying to figure out how in the world he never guessed it before. Edward noticed the decent side cut on 'his' thumb, and he had smeared the blood on his lips. He also took the tie and scarf out of his hair, and his thick brown hair now hung just above his shoulders. "He" had effectively been effaced for "she."

"Not most days, come on," James said, diving off of the top of the windmill.

She faked being hurt, to gain entry into the mansion's gates, quickly slit those guards' throats, and made her way in. Edward followed. The other questions would be answered later.

Prins was sitting in the middle of his garden, like he expected the Assassins to come for him. He put up no fight, and simply laughed in Edward's face with his final breaths. Edward couldn't revel in the moment long, James' voice echoed through the night.

"Edward! I found your man!" Edward looked up to the second story balcony to see the Sage—Bartholomew Roberts was his name—standing with James as his captive, a gun to her side. James was rather calm given the situation. Roberts and Edward taunted each other for a moment, before Edward blurted out Prins' real intentions.

"You can't trust anyone it seems," Roberts said before aiming the gun at the one bell that James and Edward hadn't disarmed. He fired, causing it to ring and alert any guards left alive. James broke free of Roberts' grip, and jumped over the rail, straight for Edward. Edward was ready to fend off anyone that he had to, to get out of there alive, and James was right alongside him doing the same.

When they were home free, and back to the windmill, they both stopped to finally catch their breath.

"Lost your man again did you?" James said, as Edward slowly walked up to her.

"Aye, Roberts is a devil with a queer aversion to kindness. I suppose that's two men I've lost today," Edward said, standing in front of James and looking square at her. "So…what's your real name then, lass?"

"Mary Read to my mum, and them I call friends. But not a word of it to anyone. Or I will unman you as well."

Edward smiled a bit. James…Mary…didn't matter what name she went by. She still wasn't having any of his shit, and he found it oddly refreshing. He simply watched her as she walked away, tying her hair up into its normal knot, before trying to secure her bandana as she walked. He still couldn't figure out how he hadn't pieced that bit of information together sooner. James wasn't James at all.

Well…that just changed everything.


	3. Chapter 3

After taking down Prins, Edward and James (Mary?) went their separate ways. Edward was in search of more keys—both Templar and Mayan—and James was off to do God knows what. Edward preferred though to not know. It was safer that way.

Standing behind his helm yet again, Edward let his mind wander. How in the world had he not figured out on his own that "James" was in fact "Mary"? Sure, her appearance had been androgynous, but Edward had just assumed maybe "James" was still young, maybe 16 or 17 at the oldest, and was striking out on his own for the first time. And with all the stories of being William Kidd's bastard son, Edward never questioned James being so well acclimated to life at sea.

But that was probably the exact reaction Mary had gone for. It worked.

Of course now that Edward thought about it, he realized Mary had to be older than he assumed based on conversations they had. Mainly, how long she had been training with Ah-Tabai. Edward hoped, for Mary's sake, either no one caught her bluff, or if they did, they kept it to themselves. They probably knew better. Edward didn't doubt that Mary would "unman" anyone who crossed her. She was spirited, that's for sure. And that wasn't an assumption based on strictly being a woman. Most other pirates and assassins were surly, brooding, angry types. Tough, no doubt, but more apt to pissing and moaning and starting bar fights. Mary was always on the go. Edward's opinion of that remained whether he was talking to a "James" or a "Mary."

Edward couldn't let himself get too lost in the politics of the world around him. He knew what he had to do, it was just a matter of taking the initiative. He had to find the Observatory. It was that or nothing. He wanted to return to England a wealthy man, and, as far as Edward knew, the Observatory would achieve that end. That was what mattered. He wanted to return home a wealthy gentleman…

Yes, maybe one day…

Edward made a hard push for the Great Inagua, and made it home in a few hours. Hedocked his ship and disembarked, happy to be back on dry land again. He headed to his house, while his crew headed to the tavern, the brothel, or the sundry small shacks that lined the beach. The bonfire was glowing brightly already, and everyone was in lively spirits. It had been a good day.

As he walked into his home, he admired the surroundings, and got to thinking about where his thoughts had trailed off when he fell asleep the night before. He had quite the set up now: Stable income, men at his command, a home that would make any nobleman back home jealous, and the general setting was beautiful. Edward had finally found the life he had always wanted. He was finally a man of quality.

He got to his office, and sat down at his desk, looking at the various notes and letters that had piled up for him. A few special steamer trunks and paintings were nearby; most likely loot from recent missions. He looked over at the armor hanging in the mysterious cell to his left. He oddly pitied the soul whose bones were now hanging there. Edward wondered maybe if du Casse had killed the poor bastard himself, or if there was more of a story to the situation than he would ever know.

But, enough of that, Edward was positive he had all of the keys, but he was too tired to be bothered with that now. He'd figure that out later. He finished sorting through his things, and headed up to his room.

The hard push to sail back home wore Edward out, even though he slept quite late today. As he laid down in bed, he felt himself sink into the mattress and pillows. Du Casse had quite the taste, for sure. But, Edward couldn't fall asleep. His mind was racing.

Home…

Home was Bristol. Home was Caroline…

He hoped, truly, to bring her out here one day, to him. Bristol and Swansea might be the world he knew, but those parts of the world held nothing for him. Not anymore. No opportunity, no hope. Just slaving away for a pittance of a wage, and no quality of life. Out here, he was important, respected, and even wealthy. It was everything he had ever wanted in life.

Edward hoped beyond hope that eventually, Caroline would join him here, as a great lady, running the house, where they lived in leisure. Maybe they would be able to make a life together, finally, and start a family.

Edward didn't even know he was asleep until he woke up the next morning. He sat up, stretched, and looked out the window. Judging by the position of the sun, it had to be well past noon. He was definitely more tired than he had been aware. He eventually dressed, and headed back downstairs to see how business was going. Not all of his ships had returned yet, and for all he knew, they had returned in the wee hours of the dawn.

He had quite the set up now. Stable income, men at his command, a home that would make any nobleman back home jealous, and the general setting was beautiful. Edward had finally found the life he had always wanted. He was finally a man of quality.


	4. Chapter 4

Some months passed, and Edward hoped from island to island, all over the West Indies. Sometimes, it was amusement, sometimes it was work. But things in the West Indies were getting tense.

First, it started with the current state of Nassau. What had once been a flourishing settlement was turning into a fetid passel of drunk swashbucklers. It was still independent and still a pirate hub. As long as those factors continued, there was hope. But not very much of it.

Then there was the issue of a pardon coming from England. Any pirates could be pardoned, free and clear, and return to Europe. Edward recalled hearing about this pardon as soon as he had landed in Havana from Woodes Rogers himself. It sounded like a good deal, but the way he had made it sound, the deal wasn't as sweet as one would thing. He wasn't lying, that Edward knew for sure, but he didn't trust the deal either.

Edward still wrote to Caroline, when he had the chance. This recent stay in the Great Inagua, he managed to write a decent letter, talking as much as he could about his excursions without giving out too much information to endanger himself or Caroline. He still didn't quite understand the Assassin's order, or what the Templars were on about, but he did realize it was sensitive business, and too much information getting out could cause needless causalities. But he wanted her to know that he cared and that while things hadn't gone according to plan, he hadn't abandoned her. Things had taken and unexpected turn.

The Inagua became a hub for Assassins and Pirates. Many of Edward's friends came and went frequently. Including Mary. Mary taught him a lot, and took a risk in helping him learn more about the Assassin's ways. She defended helping him time and time again, and Edward knew she was risking her neck for him. But she knew a lot, about the Observatory, and about the way the world worked. Edward hadn't met anyone with a view like hers before. It was a challenge, and he enjoyed it. It had been a long time since anyone had challenged him.

His feelings were changing towards her, but he kept a lid on it. Mostly for her sake. She was in a delicate position, and Edward wouldn't jeopardize it. But he did, more often than not, catch himself thinking of Mary being the one at the Inagua with him, rather than Caroline. He tried to push those thoughts out of his mind before they became too much. Sometimes, that didn't happen. But he never imagined acting on those urges or thoughts.

When Edward wasn't at the Inagua, he had a favorite tavern, The Old Avery, he spent his time at. One barmaid, Anne, was his favorite to see. Not in the way that he wanted to see Caroline again, or the ways he thought about Mary, he just liked her company. She was sharp witted, quick tongued, and took not one ounce of shit from anyone. They were fast friends, and not just in the professional sense. Edward would while away the time, talking with her, when writing his letters home didn't quite work out as he'd hoped. She was one of the few people that was neither pirate nor assassin that he called friend.

But, back to that pardon. Edward still didn't trust it, but it was obvious this was the beginning of something much more sinister. Edward wasn't sure of their exact plan, but he knew the British Crown couldn't be doing this out of a benevolent disposition. This was only going to get worse. But his preoccupation with the Observatory was of far more importance to him, than a pardon he had no intent of taking.

In the meantime, after taking on Prins, Edward took it easy. He worked on getting the whole cove fixed up. Not just his main residence, but providing other things for the sailors that passed through. And it was quite the wonder. Despite his lackadaisical attitude about most things, he was at least attentive to his home.

And Edward liked to throw parties. Pirates, Assassins, they all showed up, and many things (that will not be discussed further) happened at these parties. Edward abstained from women, but he did find himself consuming more rum than conventional wisdom would allow for. Which was then followed by getting into fist fights, and shooting matches, which meant wasting ammo. But no matter the headaches or rumbling stomach the next morning, it was always worth it to Edward. Everyone needed to blow off steam.

After one of these such parties, Mary, dressed as James, showed up, waking Edward early in the morning. He had passed out in a tree, of all places, still holding a rum bottle. Mary sighed and shook her head, but nudged Edward awake. Edward groaned, dropped the bottle, and rubbed his eyes to wake up.

"Morning Sleepy Head," Mary said. Edward rolled his eyes.

"Yeah, yeah," he answered.

"Still partying and the like until you've rendered yourself stupid from it?"

"Why not?" Edward said, tumbling from his branch. Mary laughed.

"So this is how a pirate king lives?" she questioned.

"Why not?" Edward asked. "My life, my terms. Self-made man and all that entails."

"You're just wasting everything," Mary said.

"Am I?"

"Eventually, you will."

"And who are you to say? You surely aren't my wife."

"Who ever said anything about you having a wife?"

"Um, no one…I mean…" Edward stuttered and stumbled over his words.

"Ah, I see, married are we?"

"In God's eyes, I am, but she left me some time ago."

"I understand," Mary said. "That fact may not do much to detour me, but I would hold that one close. Pirates don't have much respect for any ideals higher than plunder."

"You're definitely right about that," Edward said. Mary smiled.

"Maybe I've been wrong about you," she said. "You do have a heard and ideals after all."

"Well, let's keep that as our little secret," he said. "No, as it is, I am having yet another party tonight. And you should be there."

"I'm not sure that's a good idea, Edward," Mary said.

"Oh come on!" Edward pleaded, "It will be fun. Everyone needs to cut lose once in a while."

"I have to be in Havana—"

As Mary started her thought, Edward tried to roll swiftly out of his perch. But rather, he tumbled and crashed down, landing face first in the sand. Mary burst out laughing.

"Nevermind," she said, "for that display I will show up to the party tonight."

"Great!" Edward said, brushing the sand from his face. "I need some intelligent company around here, anyway. And, if my memories of Nassau hold, you can hold your liquor as well as any other pirate I know."

"I suppose you're right, about needing time to myself."

"That's the spirit!" Edward said, as he brushed himself off. He had a goofy, but happy, grin on his face. Mary smiled back, actually smiled. She liked the idea of spending time at Edward's hideout more than she anticipated.

That evening arrived, and in no time, the beach surrounding the hideout was littered with pirates; drinking, shouting, whoring pirates.

Mary, being who she was, had long since grown accustomed to these antics. It was easy enough to avoid joining in. There's a girl waiting somewhere for "him" or none of the girls here struck "his" fancy, and if all else fails, "there more for you lads." Those excuses generally worked with the men around her. They were usually too drunk to care, and left Mary to her devices.

Not to say she was a stick in the mud; quite the contrary really. She let loose when she could afford to, and drink until the other men wandered off with their conquests. However, that evening, Mary found herself up in Edward's home, with many others, enjoying the better selections of Edward's spirits. A few women of pleasure found their way in as well, not that it mattered any to Edward. He wasn't focused on that.

A few men were strewn out around the house. Some even invaded the guest house. Edward and Mary were in the dining room, sitting next to each other; Edward at the head, and Mary to his left.

"I'm glad you came, James," Edward said, still referring to her in the masculine around others, even if they were sauced and elbows deep in a "Dancer's" tits.

"I am too, actually," Mary answered, her hair tied up and her red bandanna masking her identity. Edward smiled a bit.

"Needed a chance to cut loose?"

"Something like that," she answered.

"Been too long since I've been able to enjoy anyone's company," Edward said, "my crew, Adé…"

"Even a woman?" Mary asked, half joking. Edward smirked.

"Even a woman."

"None of them appealing enough to you?" she asked. Then she caught herself. Maybe the alcohol was getting to her now. She never would've even considered that a question to ask, before. She swallowed the lump in her throat.

"Definitely not a question of that," he answered, "getting married changes a person."

"I can agree with that," Mary answered, "No one else ever seems…enough."

"I suppose that's one way to say it, "Edward answered, "Sometimes, there's the exception, but even then, it's no guarantee."

Mary stared at him, not sure what to say or how to react. He couldn't…

"Don't talk such shite, Edward," Mary said.

"You know I'm not," Edward said. Mary felt her face flush, but she kept her cool.

"You're a stubborn arse, and you only think of yourself."

"Yet you keep swooping in to 'save' me."

"I do not."

"You do so."

Marry huffed.

"I'm not fighting with you like a child," she said.

"But you just did."

"Shut up," Mary said, crossing her arms over her chest. Edward leaned in a bit.

"The amount of effort you exert makes a man wonder…"

"You only wonder because you know who I really am."

"Partly, yes," he answered, "but even if you were a man, it'd still be curious. No one has ever taken such an interest before."

Mary fumbled for an answer, but the words wouldn't come. And even if they did, she felt no conviction. In truth, she cared deeply for Edward, despite him being senseless, reckless, and self-serving. Deep down he was a far better man than even he gave himself credit for. Maybe that was enough for Mary.

"Alright, fine, you win…for once," Mary said.

"I know," Edward said, "now concerning _what_ I have won."

"Oh piss off," Mary said, "just because I got sentimental doesn't mean a damn thing."

"Maybe so," Edward said, "but I think you'd be lying to yourself if you said that you didn't want anything."

 _Curse him for being right_ , she thought. She had to be honest with herself. It had been far too long, period. And there were worse choices than Edward…

Nest Mary knew, Edward had wrapped his arm around her, and pulled her closer, and eventually into his lap. Mary felt her heart rate speed up, and realized how small she actually was compared to him.

"B—but…" for the first time, she stammered in front of him. For the first time, she felt shaken.

"But what?" Edward said.

"Your wife…" Mary said, surprised it was a struggle to mention even those words. Where was her conviction when she thought she would feel it the most?

"Odd moment to have a conscience," he answered, reaching up tot stroke her cheek.

Mary nuzzled his hand, her heart racing and her skin tingling. She turned her head, and, beginning to give in to her desires for Edward, softly kissed his fingertips. They were rough and hardened by life at sea; a contrast to the feel of her lips against his callouses. Edward gently ran his fingers down her neck, and a small sigh escaped her lips before he pulled her into a heated kiss.

Mary wrapped her arms around Edward and straddled his waist, her inhibitions starting to sink away. Edward ran his hands up her body, tugging at her shirt. She started rocking her hips against him, feeling him through their clothes…thick…hard…needing…

A twinge of guilt suddenly flared in Mary's stomach, as she realized where her emotions and desires were leading her. She broke the kiss, gasping.

"Edward…no…I can't…"

"Mary, please…I need you…" Edward said, burying his face in her neck, his lips brushing her skin as he pleaded with her to stay. Mary shivered, hearing Edward beg for her, but she had to find her resolve.

"No…I…Edward…I can't," she said, pulling herself from his arms. Edward disappointedly let go of her.

"I understand," Edward answered, letting her go. Mary barely looked at him as she hurried out of the house.

Edward didn't push any further. He knew that wasn't his best judgement call, but he was beginning to care less and less about that. Caroline had walked out on him first. Edward knew he hadn't always been the best husband, but he had tried. He had worked hard, and even remained faithful for all this time. He even chased this dream of riches at sea for Caroline. He wanted to give her a good life, and let her be the respectable wife and matron she'd been born to be.

She often said she was happy with how things were. Edward had a hard time believing that. Not after how she grew up. Caroline lost her station to marry him, and he wanted to give it back to her. But then she walked out…

Edward sighed and rubbed his temples. He was fed up with being the good husband to a woman who didn't care. But then he met Mary.

Now had "Mary" truly been "James" then of course, they'd most likely remain close friends James had been there to give him a swift kick in the pants when he needed it. And that happened often. But once he knew the reality, it shifted things for him.

In Swansea, Edward had always been the bad boy, or what have you. Go to the pub, get rip-roaring drunk, get into a fight, then take a pretty girl home. Edward had always passed for being older, and had his first "adventure" at 14. He was still convinced the lass he walked home knew he was young, and still a bit green, but she never let on that she knew.

He walked her home several nights thereafter. The rest is history, as they say.

Mary was yet a first. A lot of firsts. She was the first to believe in him. The first to see him as more than another peasant. The first to try and understand him. The first to capture his mind, body, heart, and soul.

Mary, meanwhile, found her way back to the pub. She was greeted by a few "Oy Kidd!" remarks, and a few offers from some of the women still looking to make a few reales that night. Mary ignored it all.

She utterly hated how she felt at that moment. She was vulnerable, exposed, and driven by passion, not reason. She had been down this road once before. Years ago. She had been married before, to a fine, upstanding man that loved her, and she loved him. She had even been carrying their child. A child that was wanted and loved from the very moment that Mary knew she would be a mother.

But then, she lost her husband at sea, and lost their child soon after. Once she recovered, she vowed never to risk herself like that again. She was on a ship to the New World as soon as her body allowed. She assumed a male pseudonym, James Kidd, and created a back story. Her mother had found herself in the midst of a night of passion with the legendary William Kidd, and James had been raised in the shadow of that legend. James had been pruned for life at sea, and was finally fulfilling his destiny in the King's Navy. But James soon had enough of that royal shit, and abandoned his post, becoming a pirate. Within a few years, he had been part of building Nassau (along with old friends and compatriots, Edward Thatch, Ben Hornigold and Charles Vane), and running with a few other former privateers, now pirates. That was when he first met Edward Kenway, a surly, boorish man who had more brains, ambition, and wit than a person like him should have. But he made it work.

Eventually James found the Assassins, quite by accident. It almost cost him his life, actually. James and one of their initiates had gotten into a hand to hand outside of a pub one night. He couldn't remember the full story, but it ended with a wrist blade to his neck, and hoping to whoever was out there he would live to tell the tale. Next James knew, Ah Tabai came out of the bushes, broke up the fight, and was impressed with James' skill. Apparently, James was a possible commodity to their cause. Ah Tabai spent the next few weeks trying to convince James to join. Eventually, James decided that he would align himself with the Assassins, to further his ideals and life here in the West Indies. The reasons the Assassins did what they did, and the reasons James forged this new life, were perfect together. James was a fast fit.

Ah Tabai, to this point, was the only person who ever knew about James' double identity. And out of respect for both James, and for their goals, Ah Tabai never let on that James was really Mary. And James was able to keep it that way.

Until Edward Kenway. Edward bleedin' Kenway.

Sure, Mary had just revealed herself as a strategic measure, and damn it worked to their advantage. But she didn't realize there would be these…repercussions. Now that Edward knew Mary was a woman, he treated her like it. Not in a belittling way. He knew Mary could shank him in his sleep, so fast he'd be dead before he could feel it. But he smiled more, he relaxed himself a little, he was kinder. The correlation was undeniable.

Sure, Edward was handsome as the devil himself, but that only carried so much weight. Many handsome men were ugly in character. Edward was no prince charming, but he had drive, passion, wit, and charisma. He had all the potential in the world, he only lacked direction. Mary tried her hardest to give him that, as she believed in him. He fought her, resisted, sometimes he even poked back at her. He was frustrating and irksome. She almost gave up on him, but she never did. Edward needed to know what kind of person he truly was.

And somewhere along the way, Mary fell hard. She couldn't pinpoint when, she just knew that one day she looked at him and her breath caught in her throat. Her heart rate sped up. Thankfully, she had quite the poker face.

Somehow, Edward saw through it, and she let him get her in a situation like the one tonight. She didn't feel violated, and he had done nothing wrong—hell she wanted everything he had done—but she couldn't risk being that vulnerable again. Not after she had worked so hard.

She paid for a room at the pub, and dashed up the stairs. When all of the windows and doors were shut and locked, Mary untied her bandanna and stripped down. She needed to remember she was a woman, even if she was going to bed alone that night. Letting her body breathe was definitely a welcome reminder.

Mary had no idea how long she slept, but when she awoke, it was midday. She dressed quickly, returned the key to the bar keep, and tried to scoot out of Edward's hideout unnoticed. She hopped on the first ship that would take her on and sailed off for Tulum by way of Havana. There was a lot that she needed to catch up on.


	5. Chapter 5

Things became hectic throughout the West Indies after that. Thatch, now going by Black Beard, was hell bent on getting medicine to help Nassau. Hornigold was ready to say to hell with it and take the pardon, and Vane was stuck in the middle on the matter. Edward had to become the peace maker, whether he wanted to be or not. Thatch put a lot of faith in Edward, and trusted what he said, so Edward did his best to reason with him. Thatch listened for a while, but only a little while. Next Edward knew, he was getting word that he had headed off to find medicine in a shipwreck. Edward caught him just before he left the dock, and got roped in to helping him out.

Thatch sent Edward on a fool's errand. First it was dive into said shipwreck, and find the cache hidden there. Edward succeeded, but the goods were spoiled. The maker's stamp was, however, intact, and lead to a chemist in Charles-towne. So next Thatch made for the Carolinas, trying to save Nassau.

Mary got wind of all of this, and heard of the role Edward was playing in all of it. She was surprised, he was the rational one for once. But she'd be lying if she didn't say she was proud of him. He was making an improvement at least. Putting someone else before himself, and trying to help a friend. It was a good story to hear?

And apparently, as far as Mary heard, Edward was successful. Thatch went off the deep end, and harassed the port at Charles-towne to the point of being a real threat, not just a nuisance. Edward was able to reason with him, and bring him around, sneak through the port settlement, raid a chemist and a doctor, and get back to the ship with the supplies intact. That was no small feat.

But, at that moment, was when Black beard started wondering about what to do next. He greatly debated taking that pardon, and returning home. Edward felt otherwise, _especially_ after risking his neck like he just did. But, Edward didn't do it as an assassin, as a pirate, as a (more or less) Englishman, he did it as a friend. He had always admired Black beard, even in their privateering days, and Black beard respected Edward's drive. Thatch knew what Edward had done for him, and backed off as soon as the medicine was in hand. But that was what made him debate whether to continue the madness of being a pirate, or to retired, and return home.

Meanwhile, once Edward returned to Nassau, the British Crown had finally had enough. A new governor, Woodes Rogers, one of the miserable bastards Edward encountered when he first arrived, had been installed there to try and…cull the problem of piracy. Some pirates had resisted the pardon, while others were still on the fence. Edward was having a hard time wrapping his head around what was going on.

No matter what was decided on an individual level, the whole of the West Indies was on lock down. Pirates all stowed away to get out, or docked their ships. Templars and Assassins alike went underground for the time being. Edward was worried about himself, about Caroline—what if someone used her as leverage? —and…even about Mary.

Edward hadn't heard a word from her directly since…that night. He didn't push either; it was for the best. He heard bits and pieces in passing, so he knew she was safe. He wanted to hear from her though, and know for sure that she was ok.

The current issues with the Crown, and having forced people underground, Edward, and several other Assassins, were holed up in the Bureau in Nassau. Of course, Edward had the Great Inagua, but it was impossible to get out and get there. And the risk to his life wasn't worth it. So he stayed put, and hid. The patrols were unusually high in number in that area of Nassau (Templar instruction, Edward was sure). He was stuck in dark, dingy rooms with little diversion.

He finally took to reading. He was only a somewhat educated man. He could read and write, of course, but his formal education wasn't much beyond that. So oddly enough, he gained a lot from the old tomes he found. Not just about the Assassins, but about the world. So many things made so much more sense now.

In the midst of one of his literary stints, Edward heard something outside of the window. Fearing the worst was about to happen, he stashed his book and crept to the window, waiting beneath the sill for whoever was trying to get in.

No sooner did someone crawl through it, did Edward lunge for them. He tackled them and pinned them to the ground. Whoever the perpetrator was, they clearly weren't expecting him to be in the room, or at the window at least. They toppled to the floor, in a heap, the guilty party letting out a surprised yell.

Edward knew that voice.

"Mary?" he said, getting up and letting her free. She sputtered as she pulled herself up, none too happy.

"Of course you dimwit," she said, angrily, "who else in God's name would scale a wall to come see you?" Edward smiled, and chuckled softly before offering her a hand up.

"I suppose you're right," he said.

"Havana is as locked down as Nassau, if not worse," she said, "I'm lucky I even got out."

Edward noticed she had come as "Mary" not "James" which made sense. The British Navy was looking for James Kidd, not Mary Read. Hiding in plain sight. Very clever.

"Well, I'm glad you're here," he said.

"I didn't want…I feared things would be the worst here, and if they were, I didn't want…"

Mary stopped herself. There she went again, being sentimental and vulnerable.

"So you _don't_ hate me for what happened at the hideout," he said.

"It wasn't my proudest moment," Mary said, "but I don't hate you.

"I'm glad," Edward said, "I should have thought it through before throwing myself at a woman like you."

"Woman like me?" Mary asked, her eyebrow raised.

"You're not like any other woman I've known. You're tough, stubborn, and don't bother with anyone's shit. Rare find, to be honest. I should have been more respectful."

"There you go, already, Edward. Trying to be sentimental again."

"And what if I am?" he asked.

"At least you know I'm not some little trollop," she said, "and I appreciate that much."

"I would hope so," Edward said, stepping in closer.

"Edward…the hell are you doing?" Mary asked, almost like she had to ask. It was a front.

"I missed you," he said, "and I'm glad you're here."

He made no further moves, besides closing the space between them. He was waiting on her for the go ahead. Mary swallowed the knot tightening in her throat.

"I missed you too," she said. Edward smiled before reaching for and holding her hand. Mary moved in closer to him.

"Evidently," Edward said, wrapping his other arm around her waist and pulling her into a kiss.

Mary wrapped her arms around Edward's neck, as she started to kiss him back, this time not pulling away from his advances. He pulled her body up against his, as he deepened the kiss. Mary felt herself melting into his arms. It was different, letting herself go, but a good difference. It was a release, not a compromise.

Edward ran his hands over her body, and started to push her jacket off. Mary helped him by shrugging her shoulders out of it. Hearing its gentle thud on the floor was an encouragement and Mary reached up to pull Edward's shirt off.

The more they undressed each other, the bolder they both became. Their hands searched each other, needing more from the other person. As they finished undressing each other, Edward started walking backwards towards his bed, pulling Mary's hips into his own. Mary gasped as she felt his arousal against her body; thick, hard, and needing her. She shivered, secretly enjoying the impact she was having on him.

Edward laid back on the bed, pulling Mary on top of him. She straddled his hips, braced herself on his chest and looked down at him.

"Ready, love?" he asked, holding her hips. His voice was warm and tender, loving even.

"I am," Mary answered.

"Please then, do as you will."

Mary took the invitation, steadied herself, and slid herself down Edward's cock, gasping and moaning as she adjusted to his size. Edward moaned softly as he felt her warmth encompass him.

"Oh god…Mary…" he said, still holding onto her hips, "I bet you're quite the good girl."

Hearing Edward talk to her like that got her going even more, she bit her lip playfully.

"I'm a very good girl," she said, as she started rocking her hips against him. Edward moaned louder before Mary leaned in and kissed him. He started grinding with her, finding their rhythm, and pace. Mary deepened the kiss, his responses encouraging her even more. She moaned into their kisses, moving faster, needing more of him.

She broke the kiss, and sat up straight, holding on with her legs to keep up the momentum. From that angle, she felt more of him, and moaned louder. Edward held her down, and arched his hips into her.

"Edward!" she gasped out.

"Louder love," he said, "tell the whole world who's pleasuring you."

"Fuck…EDWARD!" she screamed out, feeling him in just the right ways. Her body started shaking as she grew closer to her climax. She ran a hand down her body, and started playing with her clit.

"You are a good girl," Edward said, reaching up to cup her breasts in his calloused hands. Mary moaned louder as he began to massage them while she pleasured herself.

"Always a good girl," she moaned, as she continued to work herself harder and faster.

"And good girls cum nice and hard for the man they're pleasuring, don't they?"

"Y-yes sir," Mary answered. She was getting off as much on how he talked as she was with what he was doing to her.

"Edward…god…I—I'm cumming!" Mary screamed out as she felt her body burst forth. She continued riding out her pleasure until her body could handle no more. She collapsed on top of Edward in a heap. He held her close and kissed the top of her head.

"You feel better, don't you?" Edward asked. Mary nodded her head.

"I do; it's been…far too long."

"That doesn't have to be an issue now."

"Oh so you want a repeat performance?" Mary asked.

"Gladly," Edward said, "besides, right now, you're the only one who has finished."

"You have a point," Mary said, smiling, "So what are you going to do about it?"

"So, it's like that then, is it?" Edward answered playfully. He grabbed her and flipped her on her back. Mary gasped in surprise, but didn't stop him.

"You got to use me how you wanted, now I get to use you how I see fit."

"Well then, please, get started," Mary said.

Edward pulled her into a passionate kiss, holding her body close to his. She felt almost as if he were trying to possess her; claim her as his own.

He traced his fingers down her body as he started kissing her neck. Mary moaned softly as she dug her finger nails into his back. He moaned out as he continued to work his way down her chest. Mary arched her hips up to him, almost like she was begging.

"Already wanting more," Edward said, "greedy girl, or maybe, I'm just that good."

Mary could barely answer, the desire pulsing in her veins flooded her mind.

"Please," Was all she could manage. Edward smiled as he nuzzled her breast, and positioned his hips between her legs.

"Gladly, love," he said, before wrapping his lips around her nipple, suckling softly, and thrusting into her.

Mary screamed out, holding onto him as he sped up. Edward swirled his tongue around, flicking gently with it before biting down, arousing her even more. His hands wandered over her body as he thrust deeper and harder against her.

Mary's body was shaking with pleasure. It had been far too long for her, and even longer since she'd had a man as skilled as Edward. And she needed him, badly. Even for Edward, it had been far too long since he had pleased a woman. Not for lack of opportunity, but a sense of duty to Caroline.

So what made Mary different? Edward was still as married as ever, but Mary had been there for him and treated him like a worthwhile person. She'd believed in him, when not even Caroline had. He'd grown to care for her, not just as a compatriot, but on a deeper and more intimate level. She was invested in him, and wanted the best for him. He wasn't even sure if he ever could have said that for Caroline.

And Mary, well, to put it simply, was tired of coming in second to a woman a world away. She was the one here, now, hanging her neck out there for Edward. Morals be damned.

Feeling Mary's body tremble and tighten even more brought Edward back around to the moment. He looked down at Mary, admiring her beauty as she was lost in the moment. He got a charge out of knowing _he_ was the one doing this to her. Not anyone else. He leaned in closer and whispered against her lips:

"Do it again, love."

Mary didn't need any more than that. She screamed out, her body gushing in pleasure. Edward gasped out, and couldn't hold out any longer. He thrust deep inside of her, filling her body with his seed as his pleasure rolled through his stomach.

Edward pulled Mary close, and kissed her softly as they finished, their bodies slowing down together. Mary gasped as she held on to Edward, and began coming down. Edward pulled out, and laid down next to her, still holding her. Mary curled up next to him, taking everything about the moment in; how it felt, laying in his arms, how he smelled, how her body felt so wonderfully exhausted.

"You're so beautiful, Mary," Edward said to her as he watched her enjoy the afterglow. She looked up at Edward and smiled.

"Shut it, Kenway," she said. Edward chuckled before leaning in to kiss her.

They weren't lying in bed long, when a knock came from the door. Mary scrambled to hide under blankets (no one could know her real identity), and Edward almost didn't find his pants. He fortunately did, and rushed to answer the door.

"Yes?" he said, barely sticking his head out of the door.

"A letter, Mr. Kenway," was all the courier said.

"Thank you," Edward said, taking it and ducking back into his room.

"What is it?" Mary said, sitting up.

"A letter…from Caroline," he answered, reading it as he sat down on the edge of the bed. Mary moved up next to him as he read.

"Is everything alright?" she asked, leaning her head on his shoulder. Edward read for a moment before answering.

"Fine," he said, getting up, finding his shirt, and pulling it on. "You'd better go, Mary. I'll watch until it's clear for you to go.

Mary couldn't imagine what had been said, but it clearly bothered him Mary got up quietly, and got dressed. Edward was standing by the window.

"You've got about 3 minutes until the patrols came back by to get out of here, undetected," he said.

"Alright," Mary answered. She didn't say anything as she climbed out the window and made her way down the wall. When she got to the ground, she looked up to the window, and saw Edward standing there. He slightly bowed his head before disappearing inside. Mary sighed, but before she could get too upset, she saw the patrol coming. She could worry about her emotions later.


	6. Chapter 6: Caroline's Letter

My Dearest Edward,

I know the years have been less than kind to us. And, I admit, I have played my part in that. You were only trying to do better for us, and do right by me. I see that now.

It was easy then to see you as selfish and reckless. Maybe even arrogant. I thought you were trying to prove your worth, or some such nonsense, and it was frustrating to me. I was happy with you as you were; because you weren't some highbrow gentleman. You were…you. But you were also trying to be a better version of you. I was wrong to discourage you.

We were young and foolish then. We both acted too soon, and thought too little. If I had it all to do again, I would have been more patient. I'm sorry for how things turned out.

Your loving wife,

Caroline


End file.
